We've all heard rumors about these shenanigans.
"I roll Diplomacy to convince the king he's an imposter. Nat 20! Excitable shrieking! Hail to the new king!"
Clearly, that ain't the way it works. But I'm curious if this sort of stuff actually happens in practice. Have you ever encountered the phenomenon of “I rolled a 20 so [insert goofy thing here] happens?” What was the situation? Did the player ultimately succeed, or were they in for a reality check?
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I generally allow characters to add a bit of flavor to any skill check they roll a natural 20 on, or add a bit myself just to make the occasion note worthy. If it is in combat, such as with Acrobatics or Use Magic device, I go as far as to allow the action to cancel out an attack of opportunity that might have been coming their way during said action.
Mostly, I try to make things align towards the best possible outcome for the players when they roll a natural twenty, but you aren't breaking or changing reality with one.
not DnD/Pathfinder, but Earthdawn, a character rolled an 87 on a perception check using a d8, I made him go catatonic for awhile as he perceived things mortals were not meant to, but afterwards I essentially just gave them the answers to most of the mysteries as concerned the current scenario; who the Horror was masquerading as, who was Horror-touched, who stole the True Elements, etc, etc...
A fetchling in a Myhtic game I was running, rolled a nat20 on stealth with all their abilities and doo-dads running and the result was in the 60s, so I had him accidentally step into the Plane of Shadow and then opened up the optional racial trait for him early because of it.
The PCs had routed a bunch of kobolds deep in the Verduran Forest and came across a prisoner tied up in a cell. It was a Fyr (3PP fey, like a small satyr). The ranger rolls Knowledge-Nature to ID it. 20. So I ask him to roll to confirm the crit. 20. uh...roll again? 20. again? 5.
"You've met. He's a Fyr called Quill. He sells jewelry in Tacken's Bridge and made your friend Yale's wedding ring."
The group was railroaded into being captured by drow. One session later they woke up in an anti-magic cell, with their gear removed. The barbarian, with a single level of rogue, decided she'd try to pick the door, without any tools. Natural 20. Alright.
The door swung open, a duergar jailor approached them, they killed him. Drow soldiers and priestesses poured into the prison. Even without gear, the party put up quite a fight, the prison break lasted a whole session. Ultimately, they were overwhelmed by magic and surrendered or dropped unconsciously to the ground.
So they were back to square 1 at the end of the session? Not exactly. I thought they rather want a prison break instead of what I had in mind, so the drow house considered them too dangerous to let them work as slaves or mercenaries. Instead they smuggled them into another drow house, serving as a distraction while the house was attacked from outside.
Sometimes a good skill check can really make a difference...
a character rolled an 87 on a perception check using a d8, I made him go catatonic for awhile as he perceived things mortals were not meant to
I uh... I am familiar with this principle.
I do like the idea of giving the ideal mechanical outcome with a little extra flavor stank for additional effect.
